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US4070380A - 5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate - Google Patents

5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate Download PDF

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Publication number
US4070380A
US4070380A US05/765,618 US76561877A US4070380A US 4070380 A US4070380 A US 4070380A US 76561877 A US76561877 A US 76561877A US 4070380 A US4070380 A US 4070380A
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US
United States
Prior art keywords
furamidine
amidinophenyl
dihydrochloride monohydrate
compound
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US05/765,618
Inventor
Stanford S. Pelosi
Ronald E. White
George C. Wright
Chia Nien Yu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Chilcott Pharmaceuticals Inc
Original Assignee
Morton Norwich Products Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Morton Norwich Products Inc filed Critical Morton Norwich Products Inc
Priority to US05/765,618 priority Critical patent/US4070380A/en
Application granted granted Critical
Publication of US4070380A publication Critical patent/US4070380A/en
Assigned to NORWICH EATON PHARMACEUTICALS, INC., A CORP. OF OH reassignment NORWICH EATON PHARMACEUTICALS, INC., A CORP. OF OH ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: MORTON-NORWICH PRODUCTS, INC., A CORP. OF DE
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • This invention relates to the compound 5-(4-amidinophenyl)-2-furamidine dihydrochloride monohydrate of the formula: ##STR1## and a method for its preparation.
  • the compound of this invention is distinguished by its ability to combat helminth infection. When administered by gavage as a suspension in aqueous solution to mice harboring Ascaris suum worms, this compound accomplished a 67% reduction of the worm burden at a dose of 100 mg/kg.
  • the compound of this invention can be combined in obvious forms such as suspensions and dispersions to provide conveniently administered dosage compositions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate is an effective anthelmintic agent.

Description

This invention relates to the compound 5-(4-amidinophenyl)-2-furamidine dihydrochloride monohydrate of the formula: ##STR1## and a method for its preparation.
The compound of this invention is distinguished by its ability to combat helminth infection. When administered by gavage as a suspension in aqueous solution to mice harboring Ascaris suum worms, this compound accomplished a 67% reduction of the worm burden at a dose of 100 mg/kg. The compound of this invention can be combined in obvious forms such as suspensions and dispersions to provide conveniently administered dosage compositions.
The compound of this invention is readily prepared. Currently it is preferred to prepare this compound according to the following scheme: ##STR2##
In order that this invention may be fully available to and understood by those skilled in the art, the method now preferred for making it is described.
A solution of hydroxylamine hydrochloride (5.5 g, 0.08 mole) in H2 O (15 ml) was added to a solution of 5-(4-cyanophenyl)-2-furaldehyde (16 g, 0.08 mole) in ethanol (100 ml) and stirred for 1 hour at room temperature. The mixture was cooled overnight and the solid was collected by filtration to yield 16 g (94%) of oxime.
A stirred mixture of 5-(4-cyanophenyl)-2-furaldehyde oxime (16 g, 0.075 mole) and benzene (400 ml) was heated to reflux and a solution of POCl3 (4 ml) in benzene (20 ml) was added dropwise over 15 minutes. The mixture was refluxed for 11/2 hours and filtered while hot. The filtrate was washed with 5% NaHCO3 (500 ml), H2 O (500 ml), dried over MgSO4 and Darco and filtered. The filtrate was stripped of solvent under reduced pressure to yield 10 g (69%) of 5-(4-cyanophenyl)-2-furonitrile.
Dry HCl was passed into a solution of 5-(4-cyanophenyl)-2-furonitrile (10 g, 0.052 mole) in absolute methanol (100 ml) with stirring at 10°-15° for 3 hours until saturated. The product was collected by filtration; yield: 12 g (71%). A mixture of methyl 5-(4-[imino(methoxy)methyl]phenyl)-2-furimidate dihydrochloride (12 g, 0.036 mole), ammonium acetate (140 g) and absolute alcohol (550 ml) was refluxed for 6 hours and stored overnight at room temperature. The mixture was poured onto ice, adjusted to pH 8 with NH4 OH and the solution concentrated to one half its volume. More H2 O (800 ml) was added and the product was collected by filtration. After air drying, the product was dissolved in isopropanol, adjusted to pH 3 with ethanol-HCl and ether was added until cloudiness appeared. The solution was cooled and the solid was collected by filtration to yield 9 g (83%) of 5-( 4-amidinophenyl)-2-furamidine dihydrochloride monohydrate, m.p. > 300°.
Anal. Calcd. for C12 H12 N4 O .2HCl.H2 O: C, 45.15; H, 5.06; N, 17.55; H2 O, 5.64. Found: C, 45.11; H, 5.19; N, 17.22; H2 O, 5.02.

Claims (1)

What is claimed is:
1. The compound 5-(4-amidinophenyl)-2-furamidine dihydrochloride monohydrate.
US05/765,618 1977-01-25 1977-01-25 5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate Expired - Lifetime US4070380A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/765,618 US4070380A (en) 1977-01-25 1977-01-25 5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/765,618 US4070380A (en) 1977-01-25 1977-01-25 5-(4-Amidinophenyl)-2-furamidine dihydrochloride monohydrate

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US4070380A true US4070380A (en) 1978-01-24

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185020A (en) * 1979-02-07 1980-01-22 Morton-Norwich Products, Inc. 5-(4-Nitrophenyl)-2-furanmethanamines derivatives
US4185021A (en) * 1979-02-12 1980-01-22 Morton-Norwich Products, Inc. 5-(p-Nitrophenyl)-2-furaldehyde 2-(2-hydroxyethyl)hydrazone

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3084171A (en) * 1961-10-19 1963-04-02 Abbott Lab 5-nitro-2-furylamidine and alkyl 5-nitro-2-furylimidate

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3084171A (en) * 1961-10-19 1963-04-02 Abbott Lab 5-nitro-2-furylamidine and alkyl 5-nitro-2-furylimidate

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4185020A (en) * 1979-02-07 1980-01-22 Morton-Norwich Products, Inc. 5-(4-Nitrophenyl)-2-furanmethanamines derivatives
US4185021A (en) * 1979-02-12 1980-01-22 Morton-Norwich Products, Inc. 5-(p-Nitrophenyl)-2-furaldehyde 2-(2-hydroxyethyl)hydrazone

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Legal Events

Date Code Title Description
AS Assignment

Owner name: NORWICH EATON PHARMACEUTICALS, INC., 17 EATON AVE.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MORTON-NORWICH PRODUCTS, INC., A CORP. OF DE;REEL/FRAME:004085/0126

Effective date: 19820609